(3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

Base Information

Chemical Name:(3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene
CAS No.:488099-62-3
Molecular Formula:C₂₄H₄₂O₅Si
Molecular Weight:438.68
Hs Code.:

Synonyms:(3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

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Chemical Property of (3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

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Technology Process of (3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

There total 8 articles about (3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

: [(Z)-γ-(tert-butyldimethylsilyloxy)allyl]tributylstannane

: 488099-61-2
(2R,3R)-3-(3,4-Dimethoxy-benzyloxy)-2-methyl-pentanal

: 488099-62-3
(3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;
DOI:10.1021/ol0272343

Reference yield:

: 110410-38-3
1-(tert-butyldimethylsilyloxy)-3-(tributylstannyl)propene

: 488099-61-2
(2R,3R)-3-(3,4-Dimethoxy-benzyloxy)-2-methyl-pentanal

: 488099-62-3
(3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; optical yield given as %de;
DOI:10.1021/ja8063205

Reference yield:

: 30414-53-0
methyl propanoyl acetate

: 488099-62-3
(3S,4S,5S,6R)-6-[(3,4-dimethoxybenzyl)oxy]-4-hydroxy-5-methyl-3-[(tert-butyldimethylsilyl)oxy]oct-1-ene

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / H₂; Amberlyst 15 / (R)-Binap-Ru(II)Cl₂ / methanol / 100 °C / 3102.97 Torr

2.1: LDA / tetrahydrofuran / -78 °C

2.2: HMPA

3.1: LAH / diethyl ether / 0 °C

4.1: TsOH / benzene / Heating

5.1: DIBAL-H / CH₂Cl₂ / -78 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: 75 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; Amberlyst 15; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; RuCl₂[(R)-BINAP]; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene; 2.2: Frater-Seebach alkylation / 6.1: Swern oxidation;
DOI:10.1021/ol0272343